Triethylamine → HCID 67282029, compound

HRID 515497Notes

Reaction equation

HRID 515497 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=1.[Br:16][C:17]1[CH:18]=[C:19]([C@@H:23]2[CH2:29][NH:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:20]=[CH:21][CH:22]=1.C(N(CC)CC)C>>[Br:16][C:17]1[CH:18]=[C:19]([C@@H:23]2[CH2:29][N:28]([C:2]3[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]4[CH:15]=[CH:14][N:13]=[CH:12][N:11]=4)[N:3]=3)[CH2:27][CH2:26][CH2:25][O:24]2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 67282340HCID 67282340, compound

Product 1

HCID 67282029HCID 67282029, compound

Procedure

To a solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (1.00 g, 4.49 mmol) and (R)-2-(3-bromophenyl)-[1,4]oxazepane (1.58 g, 5.39 mmol) was added triethylamine (1.36 g, 13.5 mmol) at room temperature. The mixture was stirred at room temperature for 9 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: ethyl acetate) to afford (R)-2-[2-(3-bromo-phenyl)-[1,4]oxazepan-4-yl]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (A079) as white solid (1.65 g, 83%).

Workup

  1. customThe mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluant: ethyl acetate)

Sources & evidence

ORD record
ord-2f81b592d47547b99f4aad7c2e4db3e2
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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